(3aS,6R,6aS)-6-((tert-butyldiphenylsilyloxy)methyl)-2,2-dimethyl-tetrahydrofuro[3,4-d]-[1,3]dioxol-4-ol

Base Information

• Chemical Name: (3aS,6R,6aS)-6-((tert-butyldiphenylsilyloxy)methyl)-2,2-dimethyl-tetrahydrofuro[3,4-d]-[1,3]dioxol-4-ol
• CAS No.: 138127-49-8
• Molecular Formula: C₂₄H₃₂O₅Si
• Molecular Weight: 428.601

Synonyms:(3aS,6R,6aS)-6-((tert-butyldiphenylsilyloxy)methyl)-2,2-dimethyl-tetrahydrofuro[3,4-d]-[1,3]dioxol-4-ol

Chemical Property of (3aS,6R,6aS)-6-((tert-butyldiphenylsilyloxy)methyl)-2,2-dimethyl-tetrahydrofuro[3,4-d]-[1,3]dioxol-4-ol

Chemical Property:

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Technology Process of (3aS,6R,6aS)-6-((tert-butyldiphenylsilyloxy)methyl)-2,2-dimethyl-tetrahydrofuro[3,4-d]-[1,3]dioxol-4-ol

There total 2 articles about (3aS,6R,6aS)-6-((tert-butyldiphenylsilyloxy)methyl)-2,2-dimethyl-tetrahydrofuro[3,4-d]-[1,3]dioxol-4-ol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

(3aR,4S,6R,6aS)-6-(hydroxymethyl)-2,2-dimethylperhydrocyclopenta[d][1,3]dioxol-4-ol (4099-88-1,67814-68-0,70266-87-4,76249-50-8,76249-51-9,93451-15-1) + tert-butylchlorodiphenylsilane (58479-61-1) → (3aS,6R,6aS)-6-((tert-butyldiphenylsilyloxy)methyl)-2,2-dimethyl-tetrahydrofuro[3,4-d]-[1,3]dioxol-4-ol (138127-49-8)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 50 ℃; for 1.5h;

DOI:10.1021/jo991898h

Reference yield:

(3aS,6R,6aS)-6-(hydroxymethyl)-2,2-dimethyl-tetrahydrofuro[3,4-d]-[1,3]dioxol-4-ol (4099-88-1,67814-68-0,70266-87-4,76249-50-8,76249-51-9,93451-15-1) + tert-butylchlorodiphenylsilane (58479-61-1) → (3aS,6R,6aS)-6-((tert-butyldiphenylsilyloxy)methyl)-2,2-dimethyl-tetrahydrofuro[3,4-d]-[1,3]dioxol-4-ol + (3aS,6R,6aS)-6-((tert-butyldiphenylsilyloxy)methyl)-2,2-dimethyl-tetrahydrofuro[3,4-d]-[1,3]dioxol-4-ol (138127-49-8)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 2h; Overall yield = 47 %; Overall yield = 498 mg;

DOI:10.1021/jo401845q

Reference yield: 95.0%

[bis(acetoxy)iodo]benzene (3240-34-4) + (3aS,6R,6aS)-6-((tert-butyldiphenylsilyloxy)methyl)-2,2-dimethyl-tetrahydrofuro[3,4-d]-[1,3]dioxol-4-ol (138127-49-8) → Acetic acid (4R,5S)-5-[(R)-2-(tert-butyl-diphenyl-silanyloxy)-1-formyloxy-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl ester

Guidance literature:

With iodine;

DOI:10.1021/ja9843270

upstream raw materials:

(3aR,4S,6R,6aS)-6-(hydroxymethyl)-2,2-dimethylperhydrocyclopenta[d][1,3]dioxol-4-ol

tert-butylchlorodiphenylsilane

(3aS,6R,6aS)-6-(hydroxymethyl)-2,2-dimethyl-tetrahydrofuro[3,4-d]-[1,3]dioxol-4-ol

Downstream raw materials:

3,4-O-isopropylidene-6-O-tert-butyldiphenylsilyl-2-deoxy-D-arabino-hex-1-enopyranosyl 1-carba-2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside

3,4-O-isopropylidene-6-O-tert-butyldiphenylsilyl-β-D-galactopyranosyl 1-carba-2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside

6-O-tert-butyldiphenylsilyl-β-D-galactopyranosyl 1-carba-2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside

tert-butyl-{2,2-dimethyl-6-[2-(2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-ethyl]-3a,7a-dihydro-4H-[1,3]dioxolo[4,5-c]pyran-4-ylmethoxy}-diphenyl-silane

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